Inter- and innermolecular reactions of chloro(phenyl)carbene

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4819-4832

  Rosenberg, Murray G ^b   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b BINGHAMTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOLYSIS; REACTION KINETICS; SOLVENTS; SUPRAMOLECULAR CHEMISTRY;

INNERMOLECULAR REACTIONS;

AROMATIC COMPOUNDS;

AZIRINE DERIVATIVE; CARBENOID; CHLORO(PHENYL)CARBENE; CYCLODEXTRIN; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; HYDROPHOBICITY; MOLECULAR INTERACTION; MOLECULAR STABILITY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0038617299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026521h     Document Type: Article

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175. See the Supporting Information, Scheme S9.
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188. For a related example employing X-ray diffraction upon a crystalline diazirine@CyD IC, see: Bobek, M. M.; Giester, G.; Kählig, H.; Brinker, U. H. Tetrahedron Lett. 2000, 41, 5663-5667.
189. See the Supporting Information, Figure S5.
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194. See the Supporting Information, Figure S7.
195. (s) were also considered. However, both of these strategies were rejected in favor of using an aqueous alkaline buffer to neutralize the HCl byproduct.
196. 13C CP/MAS NMR: (a) Ripmeester, J. A. J. Inclusion Phenom. 1988, 6, 31-40. (b) Garces, F. O.; Rao, V. P.; Garcia-Garibay, M. A.; Turro, N. J. Supramol. Chem. 1992, 1, 65-72.
197. 13C CP/MAS NMR: (a) Ripmeester, J. A. J. Inclusion Phenom. 1988, 6, 31-40. (b) Garces, F. O.; Rao, V. P.; Garcia-Garibay, M. A.; Turro, N. J. Supramol. Chem. 1992, 1, 65-72.
198. See the Supporting Information, Figure S9.
199. -1. See: Guo, Q.-X.; Luo, S.-H.; Liu, Y.-C. J. Inclusion Phenom. Mol. Recognit. Chem. 1998, 30, 173-182; Chem. Abstr. 1998, 128, 270367.
200. -1. See: Guo, Q.-X.; Luo, S.-H.; Liu, Y.-C. J. Inclusion Phenom. Mol. Recognit. Chem. 1998, 30, 173-182; Chem. Abstr. 1998, 128, 270367.
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213. See ref 77, p 64.
214. Note that UV-A (λ = 320-400 nm) penetrates more deeply into the skin than UV-B (λ = 280-320 nm); see: Reisch, M. Chem. Eng. News 2002, 80 (25), 38.
215. 2(1) trap!
216. Calculated from 3.71 g anhydrous basis.
217. H/ppm = 4.72 (0.42 H, d J 7.8), 4.83 (0.42 H, d J 6.4), and 4.90 (0.16 H, d J 7.8).
218. In contrast to the sole 20ib signal at δ ppm = 41.0, two peaks were resolved for (R*,R*)-20ib and (R*,S*)-20ib at δ ppm = 69.47 and 69.54.
219. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939-1946.
220. Baddeley, G.; Chadwick, J.; Taylor, H. T. J. Chem. Soc. 1954, 2405-2409.
221. Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron 2001, 57, 1663-1670.
222. Two carbons.
223. A rubber band was used to fasten a paper towel covering.
224. See the Supporting Information, Figures S2 and S6.
225. See the Supporting Information, Figure S3.
226. -1. This is 1 order of magnitude below expectation.
227. 3 in distilled water to afford 1 L of solution.
228. See the Supporting Information, Figure S4.
229. See the Supporting Information, Figure S8.
230. Tee, O. S.; Fedortchenko, A. A.; Soo, P. L. J. Chem. Soc., Perkin Trans. 2 1998, 123-128.
231. See the Supporting Information, Figure S10.